Even though it’s already snowed a couple times, the daylight hours have dwindled significantly, and the Packers regular season is almost over, today is technically the first day of winter. Yes, the season most of us dread finally started today. Though winter’s arrival officially ushers in a cold, harsh, and emotionally-testing period of inactivity that lasts until mid-March, Milwaukee has made sure to combat the seasonal doldrums with a ton of great shows in recent years.

The city will once again be abuzz with a steady helping of top-tier touring comedians and bands, stacked local shows, and even a festival or two thrown in for flavor. If the prospect of another Wisconsin winter has you down in the dumps, here are 23 standout events that might help warm your spirit.

Friday, December 22 and Saturday, December 23
Void Camp @ Cactus Club
Whoa! How did we miss this until now? Over the course of two nights this weekend, Void Camp will feature a reunion show by Slow Walker, somewhat rare appearances by the likes of Convert and Astral Hand, a set by Apollo Vermouth, and more. If you’re staying in town this weekend, get to Cactus Club!

Wednesday, December 27
Milwaukee Record presents ‘The Fugitive’ @ Avalon Theater
All right, listen up, ladies and gentlemen, we’re screening 1993’s The Fugitive at the Avalon Atmospheric Theater on Wednesday, December 27. Runtime of the film is 130 minutes. What we want from each and every one of you is to share this news with every gas station, residence, warehouse, farmhouse, henhouse, outhouse, and doghouse in the area. Reserved-seating tickets to the 8 p.m. screening are $11, and are on sale NOW. Go get ’em.

Friday, December 29
The Eradicator + Avenues, William Covert, Mertles Acres @ X-Ray Arcade
Have yourself a merry little Squashmas at X-Ray Arcade this month. The Eradicator—a punk rock project based on a popular series of sketches by The Kids In The Hall—will stuff your stockings with awesome/hilarious songs about the sport of squash, the pity he feels for pussheads, and more. Eradicator gets local support from Avenues, William Covert, and Mertles Acres.

Friday. December 29 through Sunday, December 31
Nate Craig @ The Laughing Tap
While he’s now based in Los Angeles, Wisconsin-born comedian/actor Nate Craig returns to his home state with some regularity. After opening for Bill Burr at Fiserv Forum in October and headlining a Turner Hall show in November, Craig will come back to Milwaukee for his annual year-end residency at The Laughing Tap. He’ll perform a total of five shows from December 29-31, including a pair of New Year’s Eve sets.

Friday, January 5 and Saturday, January 6
Sean Patton @ The Laughing Tap
Comedian Sean Patton has performed on network television talk shows like Late Night with Jimmy Fallon and Conan, been a frequent fixture on Comedy Central stand-up showcases (including his own half-hour), released a few outstanding comedy albums, and has likely been a memorable guest on some of your favorite podcasts. Patton has also become something of a frequent Milwaukee visitor, thanks to the fine folks at Milwaukee Comedy booking him in recent years. He’ll come to the Milwaukee Comedy-owned and -operated Laughing Tap in Walker’s Point for a total of three shows spread over the course of two nights.

Saturday, January 6
Milwaukee Record presents N/A Day @ The Cooperage
Our “Dry January Beverage Festival” returns to The Cooperage to give people an opportunity to enjoy unlimited samples of refreshments from the wide-ranging, ever-evolving, and rapidly-growing non-alcoholic drink market. TICKETS ARE AVAILABLE NOW! The N/A Day lineup includes non-alcoholic beer and seltzer, kombucha, mocktails, non-alcoholic wine and spirits, tonics, craft soda, sparkling water, coffee, energy drinks, CBD products, and more. Here’s the full vendor lineup!

Friday, January 12 and Saturday, January 13
Goblin King Masquerade Ball @ Turner Hall
Awkward Nerd Events will once again transform Turner Hall Ballroom into a magical world of fantasy. There will be themed cocktails and mocktails, performances from The Goblin King Players, a custom curated drag show, and more during this two-night event.

Friday, January 19
Starcadian + Immortal Girlfriend @ Dresden Castle
What’s better than getting a somewhat rare opportunity to see Milwaukee-based sibling synth duo Immortal Girlfriend? Seeing ’em open up for Starcadian! And what could be better than that? Seeing them both at a so-called “castle” in Cudahy. It’s safe to say opportunities like this don’t come around very often, so don’t miss it.

Saturday, January 20
Napoleon Dynamite 20th Anniversary Cast Reunion @ Pabst Theater
Has it really been 20 years since Napoleon Dynamite came out? Gosh! That cruel reminder of your mortality is made slightly better with this live event that features a screening of the film and a Q&A with the actors who played Napoleon, Pedro, and Uncle Rico.

Saturday, January 27
The Championship + Christopher Porterfield @ The Cooperage
Following a reunion performance during a benefit concert for the great Lee Olson in November, The Championship is back at it again! Catch the seminal Milwaukee indie-folk outfit when they head up a Cooperage concert that also features Christopher Porterfield.

Saturday, February 3
Mitten Fest @ Boone & Crockett
It’s the same great great winter festival, only (temporarily) in a new location (for one year, so stop whining). Mitten Fest 2024 will take place outside Boone & Crockett, just a few miles up the road from its regular home outside Burnhearts. Again, the venue change is a temporary one, as Burnhearts owners B.J. and Jess Seidel wanted to take a year away from hosting the ever-growing block party “to re-envision [their] location.” We’re told the beer selection and brandy-based drink list, the eclectic blend of local music, and the lineup of area food/retail vendors will be the same as usual, so bundle up and get to Boone & Crockett on February 3.

Graham Hunt + Rustbelt, Shontrail, DJ Yuppie @ Cactus Club
Even though Mitten Fest won’t be in Bay View on February 3, the neighborhood is still playing host to one hell of a show that night. Madison (by way of Milwaukee) treasure Graham Hunt celebrates the release of a new album at this stacked Cactus Club show that doubles as an EP release show for Rustbelt and features new Milwaukee Record favorite Shontrail opening things up.

Keith Sweat + SWV, Pretty Ricky @ Fiserv Forum
Longstanding R&B legend Keith Sweat is coming to Fiserv Forum as part of his “Make It Last Forever 35th Anniversary” Tour and he’s bringing SWV and Pretty Ricky along with him. Who can entertain you like Keith? Nobody.

Saturday, February 10
The Record Company @ Turner Hall
We all know about The Record Company by this point. The Grammy-nominated band that’s fronted by Milwaukee ex-pat Chris Vos previously sold out Turner Hall and is now ready to return to town for another go-round in the downtown ballroom.

Tuesday, February 13
The Kills + The Paranoyds @ The Rave / Eagles Club
The Kills! In Milwaukee! Nice!

Matthew Sweet @ Shank Hall
Veteran singer-songwriter Matthew Sweet will swing by Milwaukee the night before Valentine’s Day to play an intimate set at Shank Hall that’s sure to feature material that spans various points of his prolific career.

Thursday, February 22
Margaret Cho @ Pabst Theater
Influential comedian, actor, and anti-racism activist Margaret Cho has amassed an astounding career that’s spanned roughly 35 years. Along the way, her unique perspective and inimitable voice have made the leap from comedy club stages to the realms of film, television, and animation. Cho will make her way to Pabst Theater for a can’t-miss performance.

Saturday, February 24 and Sunday, February 25
Burn Bright MKE @ X-Ray Arcade
Adding to the region’s ever-improving winter festival landscape is a brand new two-day affair called Burn Bright MKE. The first-year fest was created by DIY booking wunderkind JJ Kaiser, who aims to “showcase some of the best up and coming bands in the emo/alternative space” at X-Ray Arcade with two days of performances that feature the likes of Ben Quad, Carly Cosgrove,  Charmer, Heart To Gold, Saturdays At Your Place, Equipment, TRSH, Arcadia Grey, and more. YES!

Sunday, February 25
Bruce McCulloch: Tales Of Bravery And Stupidity @ Shank Hall
Accomplished actor, director, and beloved cast member of The Kids In The Hall Bruce McCulloch will treat Shank Hall to his “Tales Of Bravery And Stupidity” one-man show that’s sure to bring information, emotion, and loads of laughs to the East Side club. When a KITH cast member comes to an intimate Milwaukee venue, you go! That’s the rule.

Friday, March 1
Diet Lite + Motel Breakfast, Ladybird @ Vivarium
Mere days after officially opening, Pabst Theater Group’s latest venue, Vivarium, will host three excellent Milwaukee acts on its brand new stage. Check out the new digs and catch Diet Lite, Motel Breakfast, and Ladybird in the process.

Monday, March 4
Aimee Mann + Jonathan Coulton @ Turner Hall
You know her. You love her. She’s Aimee Mann and she’s coming back to Milwaukee (the city that inspired her and Ted Leo to start The Both). It’s going to be great.

Thursday, March 7
The Dollyrots + Gymshorts @ X-Ray Arcade
During the band’s 20-plus-year run, The Dollyrots have released more than a dozen albums and EPs, played all over the world, performed with countless punk and rock and roll mainstays, and had their music featured on television shows and in films. Just shy of a year after playing at X-Ray Arcade, the veteran pop-punkers will come back to Cudahy for a stop on their “Spring Fling 2024 Tour” with special guests Gymshorts.

Saturday, March 16
Olivia Rodrigo + Chappell Roan @ Fiserv Forum
What’s there to say about Olivia Rodrigo that hasn’t already been said about thousands upon thousands of entertainment outlets and millions upon millions of fans around the planet? On the off chance this is the first you’re hearing about this show, allow us to let you know the worldwide music/cultural sensation is coming to Fiserv Forum on March 16 as part of her GUTS tour. Make sure to show up on time because opener Chappell Roan is pretty great, too.

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.